Modern drug discovery mandates the rapid and modular assembly of increasingly complex substances. Medicinally relevant molecules overwhelmingly bear nitrogen functionality with 910 of 1086 FDA small molecule drugs contain at least one N-atom. Increasingly, the nitrogen atom is not merely a functional substituent, such as a pendant amine or linking amide, but is present in the form of a heterocycle, often bearing stereocenters. The development of methods to access these heterocycles from easily accessible precursors is an attractive goal. The resultant heterocycles will facilitate the pace of drug discovery, with the common motifs visible in biologically active agents ranging from antibiotics, antidepressants as well as agonists and antagonists of protein-protein interactions such as Hsp40-Hsp70. The specific goals of this research are as follows: 1) Develop new Rh(III) catalysts for C-H activation of enoxyamides; 2) Investigate the activation of Csp3-H bonds for heterocycle synthesis; 3) Interrogate the convergent assembly of piperidine scaffolds by [4+2] approaches; 4) Create multi-component approaches to access five and seven membered N- heterocycles. The long-term impact of this science is to enable chemists to rapidly assemble complex structures with high efficiency.